Triphenylphosphine → 7-(3-(Ethylsulphonyl)propoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline

HRID 454101Notes

Reaction equation

HRID 454101 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([O:24][C:25]3[CH:26]=[C:27]4[C:31](=[CH:32][CH:33]=3)[NH:30][C:29]([CH3:34])=[CH:28]4)=[N:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:35][CH3:36].[CH2:37]([S:39]([CH2:42][CH2:43][CH2:44]O)(=[O:41])=[O:40])[CH3:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:37]([S:39]([CH2:42][CH2:43][CH2:44][O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([O:24][C:25]3[CH:26]=[C:27]4[C:31](=[CH:32][CH:33]=3)[NH:30][C:29]([CH3:34])=[CH:28]4)=[N:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:35][CH3:36])(=[O:41])=[O:40])[CH3:38]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 129433033-(Ethanesulfonyl)propan-1-olHCID 1357631087-hydroxy-6-methoxy-4-(2-methyl-1H-indol-5-yloxy)quinazoline

Product 1

HCID 220305687-(3-(Ethylsulphonyl)propoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazolineYield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl azodicarboxylate (117 mg, 0.67 mmol) was added in portions to a solution of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (120 mg, 0.37 mmol), (prepared as described in Example 49), and 3-(ethylsulphonyl)-1-propanol (74 mg, 0.48 mmol) in methylene chloride (3.5 ml) and triphenylphosphine (176 mg, 0.67 mmol). After stirring for 2 hours at ambient temperature, the residue was poured onto a column of silica and eluted with ethyl acetate/methylene chloride (1/1) followed by methylene chloride/methanol (97/3 followed by 95/5). After removal of the solvent under vacuum, the residue was triturated with ether, filtered and dried under vacuum to give 7-(3-(ethylsulphonyl)propoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (93 mg, 55%).

Workup

  1. additionthe residue was poured onto a column of silica
  2. washeluted with ethyl acetate/methylene chloride (1/1)
  3. customAfter removal of the solvent under vacuum
  4. customthe residue was triturated with ether
  5. filtrationfiltered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-4c91bd87dc084929b8cc975b4d987d61
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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